Podcast Summary: So Money with Farnoosh Torabi

Episode 1901: How to Ask the Best Questions to Rise in Your Career (Replay)
Original Air Date: November 5, 2025
Guest: Danielle Robay (Journalist, host of Pretty Smart podcast)

Episode Overview

In this replay episode, Farnoosh Torabi interviews Danielle Robay, a journalist and host of Pretty Smart. The conversation centers on the transformative power of curiosity and asking good questions in one’s career. Danielle shares her journey from moving to LA with almost no money, leveraging curiosity to open doors, finding mentorship with the legendary Larry King, and the power of rewriting the stories we tell ourselves about money and work. The episode also delves into financial realities in Hollywood, creating your own opportunities, and Danielle’s experience with egg freezing.

Key Discussion Points & Insights

Danielle’s Early Career & Embracing Curiosity

[06:26-09:40]

• Danielle moved to LA from Chicago at 22, living in a garage with $8,000 saved. She credits an "instinct and deep knowing" that she'd succeed, though she didn’t know in what capacity.

• To break in, she cold-emailed people, sent gifts, and kept following up. Four months in, a contact invited her to host a red carpet event because she’d stayed top-of-mind. She landed an exclusive with Simon Cowell, earning $25 per gig.

• Quote:
  "I just had my eye on the prize... I would go to sleep at night thinking, who do I need to meet? How can I get on this movie red carpet?" — Danielle Robay [08:53]

• Danielle “reverse engineered” journalist careers she admired (like Barbara Walters), reading their biographies and acquiring relevant skills.

Breakthrough & Mentorship with Larry King

[14:11-19:29]

• Danielle detailed her breakthrough and how she coped with setbacks. After leaving Entertainment Tonight Online (feeling misaligned with its culture), Danielle faced a professional rut and began writing down the dream interviews she wanted.
• A friend unexpectedly took her to breakfast with Larry King, who became a mentor and greatly influenced her interview style and questioning technique.
• Quote:
  "He really refined how I ask questions and my approach... He would always say to me, you need your own show." — Danielle Robay [17:30]
• Larry King’s encouragement led her, years later, to start Pretty Smart, fulfilling her vision for a meaningful interview show.

Creating Your Own Opportunities in the Modern Media Landscape

[19:28-21:06]

• The media landscape enables creators to independently launch shows and projects. Danielle and Farnoosh agree it’s vital:
  Quote:
  "If nobody's hiring you for something, go create it, because either it will be a success or eventually someone will see that you can do the thing and hire you." — Danielle Robay [19:53]

The Role of Luck & Showing Up

[23:46-24:28]

• Danielle shares a favorite quote:
  "I think of luck like a bus. The buses keep coming, but you're never gonna get on if you're not at the bus station." — Danielle Robay quoting former Microsoft president [24:28]
• Farnoosh highlights that showing up and perseverance are crucial to benefiting from lucky breaks.

Questions to Ask for Financial & Career Growth

[25:58-27:35]

• Danielle discusses the importance of questioning your personal "money story" and the limiting beliefs that come with it.

• Quote:
  "What money story are you telling yourself? What stories have you received from your family, from your friends?" — Danielle Robay [25:58]

• Farnoosh connects this to her own teachings:
  "The stories we tell ourselves about money, about a lot of things, often point to limiting beliefs. And so the next step is to question that story. Why do I believe that? How is this story serving me?" — Farnoosh Torabi [27:35]

Financial Reality & Gender Pay Gaps in Hollywood

[29:47-31:40]

• Farnoosh references Taraji P. Henson’s public statements about inequitable pay and the misconception that on-screen success equates to wealth.
• Danielle notes progress from conversations around MeToo and the emerging use of “favored nations” (equal pay) clauses, but also shares that in her experience:
  "When I was doing my show in Chicago, I got a third less than my male co-host, and my black female co-host got paid less than me." — Danielle Robay [30:06]
• Speaking out, she believes, can embolden others to demand fair treatment.

Entrepreneurial Path & Learning Financial Literacy

[32:01-33:27]

• Danielle explains that controlling her projects gives financial empowerment and motivation to learn business skills:
  "My best investment is me... With Pretty Smart, with any brand collaborations... I'm in charge of my own destiny in many ways. The upside is potentially larger, which is exciting." — Danielle Robay [32:01]
• Launching her own card game and podcast forced her to adopt spreadsheets, business plans, and manage finances for the first time.

Egg Freezing: Questions and Financial Considerations

[33:27-35:45]

• Danielle recently froze her eggs, noting the lack of public information and emphasizing the importance of asking questions—of oneself and of clinics.
• She sought advice on medical, financial, and logistical ramifications, and plans to share her list of questions publicly for others to benefit.
• Quote:
  "If you're really wanting to do something, you find a way." — Danielle Robay [35:24]

The Power of Belief & Taking Initiative

[35:47-36:19]

• Danielle and Farnoosh stress that faith in oneself, preparation, and the willingness to show up—even in uncertainty—are essential ingredients for achieving big goals.

Notable Quotes & Memorable Moments

• On Ambition & Faith:
  "No one was going to stop me. I had my eye on the prize and that's all I could think about." — Danielle Robay [07:54]

• On Learning from Mentors:
  "I learned from the king, the king of questions... He really like, refined how I ask questions and my approach and how to, when people aren't answering, how to get them to open up." — Danielle Robay [17:30]

• On Creating Your Own Platform:
  "If nobody's hiring you for something, go create it, because either it will be a success or eventually someone will see that you can do the thing and hire you." — Danielle Robay [19:53]

• On Financial Narratives:
  "I personally had a lot of limiting beliefs around money. And I now feel like, to quote Cher, I want to become the rich man that my grandparents told me to marry, but I didn't think that was possible." — Danielle Robay [02:25, 25:58]

Key Timestamps

• 06:26: Danielle moves to LA, out of her comfort zone, with limited savings.
• 09:40: First big break through persistence and clever networking.
• 14:11: Decision to move on from her “dream job” and subsequent slump.
• 17:29: Meeting Larry King and receiving mentorship.
• 19:53: Advice on creating your own opportunities if not hired.
• 24:28: The luck vs. showing up analogy.
• 25:58: Fundamental question: “What is your money story?”
• 30:06: Insight on pay gaps and “favored nations” in Hollywood.
• 33:27: The process and questions behind egg freezing.
• 35:24: Belief and willpower in pursuing goals.

Tone & Style Reflected

The conversation is candid, introspective, and empowering—a blend of storytelling and actionable insight. Both Farnoosh and Danielle are open about setbacks and learning curves, encouraging listeners to question inherited beliefs, leverage curiosity, and proactively shape their careers.

Summary Takeaways

• Curiosity is a career superpower. Asking the right questions, being persistent, and modeling after leaders you admire opens doors—even when starting from scratch.
• Luck favors the prepared. Consistent effort and being “at the bus stop” increases your chances of serendipitous opportunities.
• Challenge your personal money narratives. Re-examine stories you’ve inherited about money, success, and risk—especially as they relate to gender norms.
• Create your own opportunities. If you’re not being offered a seat at the table, build your own—which can also lead to greater financial autonomy and control.
• Ask questions at every step. Whether it’s about salary, working conditions, or medical decisions like egg freezing, knowledge is power—and often, you’re not alone in needing those answers.

For more from Danielle Robay, check out the Pretty Smart podcast and her 52 Questions card game.